Increasing the efficiency of the transannular Diels-Alder strategy via stille macrocyclizations

Organic Letters

Volumn 2, Issue 21, 2000, Pages 3317-3320

  Marsault, Eric ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013009837     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000209h     Document Type: Article

References (27)

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2. Spino, C.; Pesant, M.; Dory, Y. L. Angew. Chem., Int. Ed. 1998, 37, 3262.
3. Deslongchamps, P. Pure Appl. Chem. 1992, 64, 1831.
4. For applications in total synthesis, see: (a) Toró; A.; Nowak, P.; Deslongchamps, P. J. Am. Chem. Soc. 2000, 122, 4526.
5. (b) Bélanger, G.; Deslongchamps, P. Org. Lett. 2000, 2, 285.
6. (c) Germain, J.; Deslongchamps, P. Tetrahedron Lett. 1999, 40, 4051.
7. (d) Couturier, M.; Dory, Y. L.; Rouillard, F.; Deslongchamps, P. Tetrahedron 1998, 54, 1529.
8. (e) Barriault, L.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1997, 134, 969.
9. Toró, A.; Deslongchamps, P. Manuscript in preparation.
10. For a review, see: Duncton, M. A. J.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1999, 1235 and references therein.
11. Precursor 1 was synthesized in tour steps from but-3-yn-1-ol with a slight modification of the method of Deslongchamps et al., see: Xu, Y.-C.; Roughton, A. L.; Plante, R.; Goldstein, S.; Deslongchamps, P. Can. J. Chem. 1993, 71, 1152.
12. For the synthesis of allylic chloride 4a, see ref 4b; allylic chloride 4b was obtained from the corresponding alcohol (Corey, E. J.; Eckrich, T. M. Tetrahedron Lett. 1984, 25, 2415) by treatment with hexachloroacetone and triphenylphosphine (Snyder, E. I. J. Org. Chem. 1972, 37, 1466).
13. For the synthesis of allylic chloride 4a, see ref 4b; allylic chloride 4b was obtained from the corresponding alcohol (Corey, E. J.; Eckrich, T. M. Tetrahedron Lett. 1984, 25, 2415) by treatment with hexachloroacetone and triphenylphosphine (Snyder, E. I. J. Org. Chem. 1972, 37, 1466).
14. Ndibwami, A.; Lamothe, S.; Guay, D.; Plante, R.; Soucy, P.; Goldstein, S.; Deslongchamps, P. Can. J. Chem. 1993, 71, 695.
15. For the synthesis of allylic iodides 4c and 4e, see ref 4a; allylic bromide 4d was obtained from the corresponding alcohol (Liu, F.; Negishi, E. J. Org. Chem. 1997, 62, 8591) by bromination using the procedure given for allylic bromide 4f. For allylic bromide 4f, see: Larock, R. C.; Han, X. J. Org. Chem. 1999, 64, 1875.
16. For the synthesis of allylic iodides 4c and 4e, see ref 4a; allylic bromide 4d was obtained from the corresponding alcohol (Liu, F.; Negishi, E. J. Org. Chem. 1997, 62, 8591) by bromination using the procedure given for allylic bromide 4f. For allylic bromide 4f, see: Larock, R. C.; Han, X. J. Org. Chem. 1999, 64, 1875.
17. (a) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
18. (b) Paterson, I.; Lombart, H.-G.; Allerton, C. Org. Lett. 1999, 1, 19.
19. (a) Hodgson, D. M.; Boulton, L. T.; Maw, G. N. Synlett 1995, 267.
20. (b) Boyce, R. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 3501.
21. (c) Smith, A. B., III; Ott, G. R. J. Am. Chem. Soc. 1998, 120, 3935.
22. Ndibwami, A.; Lamothe, S.; Soucy, P.; Goldstein, S.; Deslongchamps, P. Can. J. Chem. 1993, 71, 714.
23. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
24. In all the experiments, no dimer was ever observed by MS analysis.
25. Macrocycle 14 had analytical data identical to those of the previously reported product, see ref 9.
26. Macrocycles 13 and IS had analytical data identical to those of the reported products, see: Xu, Y.-C; Roughton, A. L.; Soucy, P.; Goldstein, S.; Deslongchamps, P. Can. J. Chem. 1993, 71, 1169.
27. Barriault, L.; Ouellet, S. G.; Deslongchamps, P. Tetrahedron 1997, 53, 14937.